Sheryl Underwood on Flagrant

Summary

Flagrant Podcast: Sheryl Underwood on Flagrant

Date: July 1, 2026
Hosts: Andrew Schulz, AlexxMedia, Mark Gagnon
Guest: Sheryl Underwood

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Episode Overview

This episode welcomes legendary comedian and media personality Sheryl Underwood for a rowdy, candid, and hilarious deep-dive. The discussion spans her philosophies on relationships, leadership, her journey through the comedy world (and military service), recent experiences at high-profile roasts, and her broader thoughts on the comedy industry, culture, and representation. Infused with sharp humor, unfiltered hot takes, and personal stories, the conversation captures the spirit of Flagrant and the authenticity of Sheryl Underwood.

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Main Discussions & Insights

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1. Accountability & Relationships

(00:01–06:34)

• Sheryl starts off with a joke-laden interrogation about the hosts’ relationship statuses, then pivots to personal responsibility in relationships.
• Emphasizes the concept of "contributing to your own frustration" and self-accountability.
  • Sheryl: “I wish more bitches had it.” (01:24)
• Uses the "hair on the soap" scenario as an example of managing expectations and recognizing patterns in relationships.
• Discusses the transactional nature of relationships:
  • Sheryl: “All relationships are transactions… you’re either trading for love or comfort or security, or you make me feel good.” (05:47)

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2. Money, Gender Roles & Power Dynamics

(03:31–06:34, 12:24–13:28)

• Shares her views on being a successful woman, the perception of breadwinning, and the psychological link between a man’s financial stability and his readiness for commitment.
  • Sheryl: “When a man’s money is not stable, he cannot concentrate on a personal relationship.” (04:10)
• Even when she out-earns her partner, she prefers to "live off what you do," maintaining the man as head of household, reflecting her upbringing.
• Touches on deferring to male leadership in the family, influenced by her father’s traditional values:
  • “I’m not the boss. I’m the leader. The boss tells you what to do… The leader leads you into battle.” (13:28)

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3. Comedy Roots: From Military Cadence to the Stage

(13:53–21:42)

• Sheryl’s comedic sensibility was shaped by her military family upbringing, time in the Air Force, and church performances.
  • Early start as a singer, but comedy soon took center stage.
• Her entry into comedy included performing for troops, learning to entertain across cultures and backgrounds:
  • “When you’re talking to somebody that you never knew anything about… you still gotta crack him up.” (20:10)
• Recalls her dirty cadences during Air Force marches and the importance of military experiences on her comedic voice.

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4. Performing for the Military & the Power of Comedy

(22:01–27:13)

• Describes USO tours, performing in Afghanistan and for troops abroad with unforgettable impact.
  • Humorous anecdotes: hot pants, fringe boots, fringe jacket at a Navy base; drawing Marines to guard her due to overexcited troops.
• Comedy as catharsis for people under stress ("gallows humor"):
  • “That’s what comedy does… it brings us together.” (26:17)

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5. Roasting at Netflix’s Kevin Hart Roast and the Art of the Roast

(27:20–38:28)

• Insight into the preparation and high stakes of the Netflix Kevin Hart Roast.
• The camaraderie and competition among comics:
  • Sheryl describes working with writers, respecting the strengths and approaches of comedians like Nikki Glaser and Tony Hinchcliffe.
  • On joke boundaries: “If it ain’t funny, I’m going to get your ass!” (38:04)
• On the evolution of roasting, from Friar’s Club to televised events, and maintaining camaraderie even with savage jokes.

Memorable Moment:

• Sheryl consulting God for what to say on stage, wanting to deliver for the room and the audience. (39:58)
• “You gotta make it better… If you can’t make it funnier, leave it alone.” (35:48)

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6. Comedy Industry Dynamics & Building Opportunities

(31:38–34:10, 86:08–96:29)

• Sheryl's passion for bringing up fellow comics, especially those overlooked or past their "fame moment."
  • Her shows are designed not just to headline herself, but to pass the mic and share the stage.
  • “We run it like a house party… But we run it.” (33:08)
• On industry shifts, she urges leveraging viral moments for long-term opportunities and networks.
• Discusses the economics of stand-up, production, and how diversifying platforms (Netflix, short-form video, multimedia) is vital for the next wave of comedians and creators.

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7. Controversy and Context: Roast Backlash

(45:33–50:55)

• Addresses public outrage over roast jokes and the limits of “political correctness.”
  • "Of course the roast was racial. Of course it was. But that’s not the same as being racist." (45:41)
• Observes that outrage is often whipped up by contextless clips circulating on social—and a roast is not meant as a safe space.
  • “A roast is different than a street fight… everyone signed up for it.” (48:25)

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8. Representation, Legacy, and Paying It Forward

(91:08–96:29)

• On the pressures and responsibilities of being a Black female comic at center stage.
• The importance of using new-found platform to open industry doors for more diverse voices.
  • “That’s my job, to open the door. That’s why it’s leadership. Am I right?” (97:08)
• Praises Kevin Hart’s pivotal role as both cultural symbol and entertainment mogul in pushing the collective forward.

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9. Personal Anecdotes & Comedy Mentors

(71:31–77:48)

• Deep dive into Bernie Mac’s influence and the culture of Chicago comedy.
  • Bernie as mentor, his unique crowd control, and pivotal “Kings of Comedy” moments.
• The art of “mechanics” for comedians: cadence, crowd work, and structural mastery over just punchlines.

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10. Women, Power, and Dating in Comedy

(80:00–85:08)

• Sheryl expounds on the challenges of dating as a strong, successful, and independent woman.
• Talks honestly about male intimidation, her preference for traditional but confident men, and jokes about transactional aspects of relationships.
• “A real man looks at me as an asset. If you’re quiet as a man, but you’re still a strong man—asset.” (83:51)

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11. New Ventures & Looking Ahead

(85:08–96:29)

• Pursuing variety shows, talent search tours, and animated projects targeting young adults—“blending daytime persona with stand-up edge.”
• Commitment to giving back through foundation work and creating jobs for the next generation of performers and crew, especially in California.

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Notable Quotes & Moments

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• On Accountability in Frustration
  “I’m trying this new thing… called figure out where you can be contributing to your own frustration.” (01:13, Sheryl)

• On Breadwinning & Gender Norms
  “I make more money, but I’m not the breadwinner. The man is the breadwinner.” (03:31, Sheryl)

• On Comedy & Leadership
  “I’m not the boss. I’m the leader.” (13:28, Sheryl)

• On Performing for the Military
  “We can’t protect you. These men have been on the ship for 40 days. If you keep talking, we can’t protect you.” (23:53, Admiral to Sheryl)

• On the Roast, Preparation, and the Moment
  “I kept asking God on that stage, give me the words… that the audience needs me to say.” (39:58, Sheryl)

• On Comedy’s Power
  “That’s what comedy does… it brings us together.” (26:17, Sheryl)

• On Pushbacks and Culture Wars
  “If you push the pendulum too far to politically correctness, then people are gonna fight back.” (41:04, Sheryl)

• On Success, Opportunity, and Lifting Others
  “That’s my job, to open the door. That’s why it’s leadership. Am I right?” (97:08, Sheryl)

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Key Timestamps

• Accountability in relationships & the “soap” story: 01:11–03:15
• Money and power in couples: 04:05–06:34
• Sheryl’s comedy origin story: 13:53–19:13
• Military comedy anecdotes: 19:46–26:17
• Preparing for and reflecting on the Netflix Kevin Hart Roast: 27:20–39:58
• Debate: outrage and meaning in roast comedy: 45:33–50:55
• Mentors & Chicago comedy lore (Bernie Mac): 71:31–77:48
• Women, relationships, and strength: 80:00–85:08
• Dreams for new programming & industry impact: 85:32–96:29
• Final leadership/legacy remarks: 97:08

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Tone & Takeaway

The episode is electric, insightful, and unapologetically candid—mixing raunchy humor, industry wisdom, and hard-earned life advice. Sheryl Underwood radiates both trailblazing leadership and vulnerability, challenging industry norms around gender, power, and representation, and giving an inside look at the structures that build (and sometimes break) comedic careers. Fans and newcomers alike will find both laughter and inspiration in her stories and philosophies.

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For more, listen to the full episode for in-depth anecdotes, sharper punchlines, and the full spectrum of the Flagrant + Sheryl Underwood experience.

Transcript

[A]

Y' all might well start the camera right now.

[B]

Let it roll.

[A]

Yeah, well, I think that. Okay, there's. When you. So when you guys. All of you are married?

[B]

Yes. Yeah.

[A]

Okay.

[B]

He's not really married. He likes to pretend like he's married.

[A]

He's married.

[B]

It's that. What is this?

[A]

Y' all ladies shacking or what? Y'. All.

[B]

No, we engaged.

[A]

Engaged. Oh, okay. So you almost.

[B]

You bought a ring?

[A]

You married? Yes. Right. Okay. Got it, got it, got it.

[B]

So you.

[A]

So you married. So you. You fell in love with the girl? Uh. Oh, you fell in love with the girl. Is there anything that she does to this day that still drive you up a wall?

[B]

Like, annoys me.

[A]

Yes.

[B]

Nah, she's perfect.

[A]

You the jackpenny. You not even lying right. That ain't come out right. Side, bitches. Side, bitches. Side, bitches. So you. You going to leave her and bury me? Yeah,

[B]

of course.

[A]

I. I don't want to be with her. That's right. I'm a call. Matter of fact, I'm calling right now, bitch. Never coming home, sunshine. Okay, what did y' all want to talk about, too? Yes, we want to talk about you. From me talking to somebody that I was like, what?

[B]

Something was frustrating you. We could tell.

[A]

But here's. I'm trying this new thing. Yeah, and this new thing is called figure out where you can be contributing to your own frustration.

[B]

Accountability.

[A]

There you go. And I wish more bitches had it. How do we.

[B]

It's a new book.

[A]

It's a new book we can all write together.

[B]

Hey, people. Artists.

[A]

Hey, bitch. You had a problem. You are contributing.

[B]

We've been trying to write that book for a long time. That's not a book. This is a scientific paper.

[A]

Okay, so how do we solve this theory? How do we test it?

[B]

Well, how have you noticed that you're the problem? How can you think you're the problem when you're on fire right now? It seems like every decision you made was the right decision.

[A]

Well, I would say most. If you're 90%, it's the 10 that you need to work on. Okay, so if you're communicating with someone and they don't seem to be understanding, then the first thing I look at is because my dad taught me, look at yourself first. So am I not conveying it right? Or did I believe. Now, this is where I think me as a woman, did I believe that you were capable of doing. Of not doing what you're doing?

[B]

Yeah.

[A]

So if I believe that you were capable of not doing the thing that annoys me, then I'm the problem. Because I believed it. No, I believed that you were not gonna do the thing. If you don't like hair on soap.

[B]

Yeah.

[A]

And every time this dude comes over whose hair. It's his hair on my soap. So he taking my bar of soap and rubbing his balls with it. Can I say that?

[B]

Yeah.

[A]

Rubbing the balls with it. And then it's in my shower. But I'm in love with this dude and I go with this motherfucker with the pubic hair on my damn soap. But if I believe that he's incapable, if he's capable of not doing that.

[B]

Yeah.

[A]

Continues to do it. So either it's a challenge to authority somewhere in there. Okay. Cuz he doesn't want to be controlled. So the keep asking me about the pubic hair on the soap. And I keep telling this bitch showing this, I'mma put the pubic hair on the goddamn soap. I'm a man.

[B]

There is an ego in it which is like, stop telling me what to do.

[A]

Yes.

[B]

It's almost like you need to suggest it or ask it. But telling, there's a thing about the being told.

[A]

Well, I say, might you consider.

[B]

See, I think we look at that and we just said, yeah. She just told me what the fuck to do.

[A]

Well, see, I feel like it's the man. Remember when I was. I don't know if y' all saw me on Shannon Sharpe's Club. Shay. Shay, right. And he asked me how did I feel being the breadwinner? I'm like, I'm not the breadwinner. I'm the person who might make more money in a relationship. Depends on who the man is. But I'm not the breadwinner. The man is the breadwinner. And we live off of what you do. My money is in addition to. Hey, you want to be a cowboy? I'm going to send you to Montana to learn how to be a cowboy for your birthday. Right. That's what my money is for.

[B]

So you. When you're with a guy, you will live completely within the means of his

[A]

salary if that's what he wants to do. Well, first I got to get to being engaged or married or being that girl for you. Cause if what I believe, and I could be wrong and hit me in the comments. I believe when a man's money is not stable, he cannot concentrate on a personal relationship with a woman.

[B]

There is a version of that because it's hard to separate your identity from your ability to provide.

[A]

That's Right.

[B]

Some guys can do it, man.

[A]

What, the gigolo?

[B]

The gigolo, yes. But they have a disconnect. There's almost like a sociopathy that allows them to do it.

[A]

But then to me, God makes woman's intuition to go, that guy's a gigolo. Do I want to be with a gigolo? Or do I want to be with all these other girls that are with the gigolo? And then, because I would ask a man, how long do you plan on being a gigolo? And can you use those skills for anything else? And how can I help you? Yes, in the beginning, yes, we gonna do what we gonna do. But if you seem to be good at being a gigolo. Cause you pull me, I fell for the bullshit, so that's what you gonna do. And I got the 1500, if that's what we doing.

[B]

So what are we doing with this 1500?

[A]

That's right. How are we gonna trade? How we gonna take 750 of us or 500, put 500 in crypto, 500 trying to get your life together, and then another 500 for you to live off of. Now, you want to be in a relationship with me or this just. Is this a transaction? Which all relationships are still transactions.

[B]

How so? To me, how so?

[A]

You're either trading for love or comfort or security, or you make me feel good or you care about me.

[B]

Does it make it not transactional? If it's a love for love trade,

[A]

it's still a transaction. It's equal love. I love you, you love me, and we build a life together, it's still a transaction. It's just a more pleasant transaction. Right. If it's just, I'm fucking you because you pay me, or I'm fucking you because I get something from it or home security. That's right. That's right. To me, I wish people would just talk about it's a transaction because my needs are meeting your needs. And let's see how we can get together. And if we enjoy ourselves together. But then you gotta figure out what about the shit about me that you don't like. And then can you handle that shit? And can we just talk about it?

[B]

What's not likable about you? What could someone not like?

[A]

Ooh, it's a lot. It's a lot.

[B]

What is the thing? You smell phenomenal. You're engaged

[A]

to our guest black guy, right? But if that guy would have said, I be like, hey, man, you know? But then I'm like, for real.

[B]

He got a white wife. Don't let him fool, you.

[A]

You got a white wife, you got

[B]

a vacant, you got a vacuum.

[A]

European.

[B]

That's European.

[A]

No, but that's what you do, Little. No. Okay, listen, listen. I'm not against interracial. I have sampled everything God have made on the buffet of love. So I'm not against it. Same, Right.

[B]

What's the best. Can you rank them?

[A]

I. I would say, well, everybody's decent. If you still talking to me after we do something decent. You still talking. If you ain't put your hand in my back and said, all right. Ch, that was cool. Okay, The Knicks will be on in a few minutes.

[B]

Okay.

[A]

Is in your shoes, bitch. Why are you still here? Oh, man, I. And I get a Uber. Wait, listen. No, I had a guy. Okay, wait. See? It's a good start. So I met this guy. We've been talking on the phone for about a year. Talking on the phone.

[B]

What race?

[A]

He black, play football. And we met at a Super Bowl. And he comes up, I'm selling cassettes. That's how long ago it was. Cassettes and CDs and posters. So he comes out, how much this cost? How much does this cost? And I was like, okay, if your big ass gonna buy something, buy something. So then he says, you know, let's exchange numbers. And I said, well, you know, listen, I'm not these bitches, okay?

[B]

So straight up. Said straight up.

[A]

I said, I'm not these bitches. I'm a different bitch. If you want to exchange numbers, cool. But I'm not excited about that, right? So we start talking, and we talk, talk for months, years. I think I'm getting to know him, right? So by the time something about to happen, I'm in the city where he's playing football, and he sends a car for me. Now you just have far back, sends a stretch limo, you know, so we all looking out the window. Ooh, ah I was like, don't ooh ah don't ooh, ah. It's a setup.

[B]

It's regular.

[A]

It's a setup. No, it's a setup. I'm thinking it's a setup. I'm being set up. Okay, so it's a setup. So I get to the crib. I used to tell this story in my act where we get to the location and the limousine dude is just throwing shit out the car. Like, scared drive off. I'm like, I'm trapped in this motherfucker. But I'm glad I got gas money in case I need to get the fuck out, jump out a window or something, right? So then we get together and he says. He said, I got to go to work. I said, okay. In training camp. I said, okay, so what's up? And he said, what do you mean? I said, when's the car coming to get me to take me back? He said, Friday. I said, I'm not like this for four more days. You're in training camp, not me. I was panicking. Cause I don't have that type of duration. I was panicking, right?

[B]

So.

[A]

But then I thought about it. So then he goes downstairs, there's some money and khakis and this car garage and everything. So I go down and look at the car. Car has not been driven. And it's a guap. It's a big guap of money, right? Guap. So I look at it and I go, it's a setup. This is not right. You know, this is first day. And I get the money in the car and it's some bullshit. Must be some cameras around this motherfucker. I'm being set up, right? I never think it's the happily ever after. Never, never. So I call my father and I go, daddy. I said, I think I'm being set up.

[B]

You calling your dad from the house?

[A]

Yeah, from the house where I was in the car.

[B]

She's probably sitting there.

[A]

I called my dad. Yeah. And I said, I think I'm being set up. He said, what do you mean? And I told him what happened. You said the details? Yeah. I said, you know, we were romantic, you know. You said, my dad, right? And I said, but I said, this happened. This happened, this happened. I said, what do you think? He said, don't fuck this up until I meet my son in law. What? And then, and then when it's time for me to go back, cause it's time for him to go play with the team.

[B]

So you stayed for the weekend? Yeah.

[A]

Yeah, stayed for the weekend.

[B]

How was your body holding up?

[A]

It was a struggle.

[B]

It was a struggle. Yeah.

[A]

Cause I'm only five two, right? It was a struggle. And you 65350. Pussy had two black eyes, Popeye. I'm like, who is doing this all day? Who is doing this with you all?

[B]

He did, right?

[A]

So when it's time to go, right? So I said, so what's up? You know, what is this? I said, cause this is a lot, this seems like. He said, why don't you just relax? And then he said, I'm take you. The car's gonna take you back. I said, oh no, motherfucker, no. After five Days of this, you have to go back and you have to introduce yourself to my father and you have to talk to him. What? What? I said, motherfucker. Yeah. I said, so put some clothes on. So I made him get in the car that I didn't drive, and he drove me back to where my father was. I said, get out the motherfucking car. Go talk to my dad. So he walks in and my dad's watching wrestling. So he's sitting straight to a tv. He doesn't look up. My father doesn't look up. My father, old school Southern, right. He doesn't look up. And I said, daddy, this is such. Such and such and such. He nods at him. And then I said, why don't you just tell him what you do for a living? I play his football.

[B]

My father said, stop, Cheryl Dumbar.

[A]

My father said, you do not have to bring her back to come back and visit us. I said,

[B]

did you get that?

[A]

Now, once he say he play football, he don't give a fuck about me. It's the older daughter.

[B]

You're welcome to come here anytime.

[A]

Anytime you want. Anytime you want. So what I'm saying is, is a long story. Long as you have to figure out what is is, especially as a woman, you need to figure out what is is and what role you gonna play in this situation. And that's why I do not believe any man I date. Whether you play football or whether you work at the gas station. I'm not the breadwinner. You are the head of the household. Cause that's the way I was raised. My father was the head of the household when my father died. I defer to my older brother.

[B]

Oh, really?

[A]

Right.

[B]

But you got leader energy. I don't know. I don't believe that you completely would defer to anybody but a.

[A]

As to play the position, you could.

[B]

You could lead from behind.

[A]

Absolutely.

[B]

And.

[A]

And I, you know everybody that works with me.

[B]

Like a football player.

[A]

That's right, all of us. And he was trying. And I was scurrying. No, no, no, that's not for you. You never even met my dad. My dad didn't that. But everybody that I work with, I tell. They go, you're the boss. No, I'm not the boss. I'm the leader.

[B]

Interesting.

[A]

The boss tells you what to do, and you can be unhappy about it. The leader leads you into battle, and you will go into battle with the leader because you know we're coming back alive. And that's why I'd rather be the leader than being the boss to dictate to someone.

[B]

Is this military influence, or did you have this from, like, your pops early on or your mom early on? Like, where are you getting this philosophy on the world?

[A]

My dad really shaped my worldview. And he was military. He and all his brothers were in the army. And then my mother married a man who was stationed at Offutt Air Force Base, and that's what we're doing. So that's how we got to Castle Air Force Base and then went into the Air Force. So I was at Water High, but I always.

[B]

But wait, hold on. Didn't you. You went into Air Force later, though, right? You got your master's before that?

[A]

I was working on my master's while I was in the Air Force. So I got my associates, my bachelor's, my master's degree, a paralegal certificate from UCLA, and I have five honorary doctorates, four of them from HBCUs, one of them from University of Illino, Chicago. So I wanted to go to college because my dad was really, really smart. But my dad was. He was progressive but very conservative, you know, so he would read a lot and understand people, and I wanted to be that. And my dad and my uncles on my mother and my father's side. Very, very funny.

[B]

Yeah.

[A]

So I would just be in the corner watching them.

[B]

Like, how.

[A]

So what were you observing, absorbing storytelling cadence, hitting the joke. And I was like, okay, that's interesting, because I started out as a singer singing the choir.

[B]

No way.

[A]

Most of us.

[B]

Okay, you grew up in the church.

[A]

Church, singing the choir. So I was like, oh, maybe I could be a singer. I wanted to be in the entertainment business.

[B]

You felt it early?

[A]

Definitely. Yeah. Five years. Well, you know, you know, us community. Your parents wake you up in the middle of the night to dance for their friends and perform. Okay, he's Puerto Rican.

[B]

He's Puerto Rico. So they were partying when we were

[A]

awakening, but they never said, come, my son can pop lock and spin on his head. They never said that or you wasn't salsa dancing everybody that you didn't have no white shoes or nothing like that.

[B]

I wasn't nice to them.

[A]

Okay, so Puerto Rican, Dominican. None of that happened for, you see, when we were growing up, our parents would wake us up to perform for their friends while they playing cards and all this stuff. So I thought, okay to get that kind of attention, you know? Oh, okay. I kind of liked it. I knew I wanted to be in the entertainment business because I spent a lot of time in the house and watching things And I was like, I can do that. I can do that. But how do. What do I do? Do I start off as a singer? I don't have pipes. My voice, when I started singing, it sounded more like Diana Ross, you know? But now that I've been doing comedy for so long, it's lower. It's like Lou Ross, you know, it's deeper now. I still sort of sing. I can sing, talk. I say I can sing, talk, walk, dance.

[B]

Got it, got it. You know, quick update. I'm gonna be out in LA shooting a movie this summer, but we added some standup shows, so pull on up the Brea Improv will be there July 17th and July 18th, and then we're gonna be at the Halifax, Nova Scotia, Canada, Great Outdoors Fest August 8th. So you can go grab tickets any of those shows if tickets are still available. TheAndrew Schultz.com.

[A]

all right, Mark, what do you got?

[B]

Oh, I have great news. I'm going all over at the end of the year. I'm going to Plano, Texas, Chandler, Arizona, Pasadena, California, San Diego, California. And then I'm also going to a couple other spots that are going to be coming up at the end of the year, like Detroit, Michigan, and Salt Lake City, Utah. And I can wait. I can't wait to see you guys all there. Markagnon live.com Alex, guys, my monthly tennis series. Theall loveclub.com. the tennis is on July 25th. I'll see you guys there. The first one was fantastic. Second one's gonna be even better.

[A]

Then I got into dancing and I answered an ad while I was in college at a bar. And it was a sexual interpretive dance. That's what we call it.

[B]

Sexual interpretive dance. Yes. Sounds artist.

[A]

It's a great way of saying stripping.

[B]

Yeah, no, it's art.

[A]

I thought I was being artful. What it was. So I grew up in Chicago as a tavern. And it's still open to this day. And the owner remembers the day that I did this.

[B]

Get the fuck out.

[A]

Yes.

[B]

How old are you when you go in? Oh, I was 19, 20.

[A]

I was young. I was young, but old, you know, I was young but old. We got safe age watching this. Still my damn identity. And my credit is fucked up. No, still my identity. So I'm in this place where you're supposed to. You put on the lingerie and then you're supposed to. Yeah, so the guy. The guy buys it. So whoever buys it.

[B]

Like burlesque? No, it's a little bitty place.

[A]

Burlesque seems Beautiful. It's like a movie with. What's that Girl? Christina Aguilera and Cher. Have you seen it?

[B]

Moulin Rouge?

[A]

No, Burlesque was the movie they did together. Matter of fact, James Brolin was in the movie. But I digress. So it's more like you buy. Buy the lingerie. You walk around the little bar and whoever wants you to take it off, they pay for the lingerie. So you take it off in front

[B]

of them, and then they get to keep your lingerie, but you're naked in

[A]

front of these dudes. So it's really a fancy version of stripping. But. And I think, God, let me know what I'm not capable of doing. So I start to tell jokes. And I was doing the Fred Sanford.

[B]

I was telling jokes, doing full lingerie.

[A]

Yeah. And them straight dudes, you can't straight work the damn. Put your shit back on your tail, you know? So that's when I knew, oh, I can do it. And then being in the military, I was making people laugh in the military because you have to entertain. We had a lot of downtime, so you have to entertain. And basic training, what did you do basic? Lackland Air Force Base. Lackland was basic training. San Antonio. The tech school. Because I went in as a medic and they told me I could transfer out to mwr.

[B]

What's mwr?

[A]

Morale, Welfare and Recreation. So that's what I wanted to be because I knew I wanted to be in the entertainment business.

[B]

Wait, do you go in as an officer?

[A]

No, I went in as enlisted. But it helped me pay my way through school. But it also taught me how to entertain people. You don't know. If we're talking to each other, then we know some of the things of our background that's gonna make us laugh.

[B]

There's a shared understanding and a shared reality. But when you're talking to somebody that you never knew anything about. Absolutely. Mexican dude from El Paso, Texas.

[A]

That's right.

[B]

You still gotta crack him up.

[A]

Or a white boy from Oklahoma. You gotta make him laugh. And so I found that I was funny and I was doing the cake. Cause I was too. I couldn't do the guide on. The guide on is where you twirl the flag, but you can't. Don't let that flag hit the ground, Airman, you know, so you can't let the flag hit the ground. And they hear that. Everybody looking at you like, you crazy, right? So I couldn't do that because I don't think I had the cause. You got to twirl it under your arm.

[B]

Okay.

[A]

And I couldn't do it. But then they said, well, what else could you do? And One of the TI's said, Let her do the cadence to chants. But my chants were, you know, your mother was home when you left your right. Your mother was so. But mine were dirty. Dirty.

[B]

Oh, so you do. Okay. Okay.

[A]

Yeah. And people looked forward to us marching, but mine were dirty.

[B]

And they're trying to keep a straight face.

[A]

They're trying. That's right.

[B]

They're trying to crack them.

[A]

Do you remember any of the.

[B]

Any of the cadences?

[A]

Nothing I could say here, but I say whatever you want. One thing I do remember is that I learned that I could be entertaining, but I also learned that it takes being in the military first. It's a scary thing because they strip you down to build you back up, but it's the best thing. I wish in this country we had mandatory. And if you don't want to do mandatory military service for two years, go into Peace Corps.

[B]

Yeah, do something.

[A]

You should do something in the sense

[B]

we were talking about this, like, volunteering at the national parks or something, serving the country in some capacity. We were in Virginia beach this past weekend doing shows, and the USS Iwo Jima came back. And I'd never seen this live, but, like, you got to see the ship that was away for 10 months.

[A]

Yes.

[B]

The whole family. People with kids.

[A]

Yeah.

[B]

It's also, like, 10 months. So you see a really young baby, you're like, hold on.

[A]

Is that.

[B]

But like, dude, I got emotional, man. I got kind of caught up in it.

[A]

The music, the pomp and circumstance.

[B]

Also, just seeing these young, like these. These are kids. They're, like 21 years old. They're coming off, their moms are grabbing them. It was their first time. These, like, big hugs. And it was just this beautiful thing, asking one of the moms, like, oh, who are you here? She's like, oh, my son. And you're like, how long has he been deployed? She says, 296 days.

[A]

Oh, to the day. To the day. It was like a care packages, sending cookies.

[B]

They said Amazon replaced all that.

[A]

Yes.

[B]

If you try to send a care package, it's gonna take twice as long as. If you just go Amazon direct. And I'll find a way to.

[A]

And that's what's good about ingenuity, of course. But also, when you're away like that, you live for letters and care packages and things like that. And I remember when I was first performing after I got out of the reserve they called me, somebody called me to do a comedy show. And we were in Yakuzka Naval Base in Japan. In Japan. So I was doing my comedy has always been adult, always been sexual, always been adult, profane. So I was wearing these fringe hot pants and this fringe bolero jacket and bootstrap. And I had these fishnet stockings, these pumps on that I couldn't really walk in. And I was telling the most hardcore sexual humor. And the admiral, they said, the admiral would like to see you. And I said, sir? And he says, so you form a military. I said, yes, sir. And he said, listen, I'm gonna give it to you straight. What? We can't protect you. These men have been on the ship for 40 days. If you keep talking, we can't protect you.

[B]

When the US Military says they can't protect you, who the fuck else got you?

[A]

I know who they put in front of the cause. We were staying in Billiton, where, you know, the hotel is called Billowing. So we were staying there. You know who they put in front of my door to guard me every night? And they were in shifts.

[B]

Bruce Lee.

[A]

The Marines.

[B]

Really?

[A]

The Marines. Because these dudes were sitting outside of my door playing a guitar, making beaded necklaces and professing their love. And I was like, what is happening? What is happening? I'm just doing a show.

[B]

Yeah.

[A]

You know, but I do. I, like, perform for the military. The last thing I did, I did a USO tour.

[B]

Yeah. That's pretty cool.

[A]

Oh, my God. So fun. So fun. But what made it really fun for me, it was with the sergeant Major of the Army. And I kept asking him, are you sure you mean me? Are you sure you want me to go? Because you know me, right? And the USO people are like, absolutely. Because you don't get paid for it. The payment is the love from the troops.

[B]

Yeah.

[A]

So we go to Afghanistan.

[B]

Whoo.

[A]

And we go down to the fobs. Well, first, I'm so excited. I think I'm going to walk up to General Petraeus and I'm going to shake his hand and hug him and tell them how greater is Jim. Petraeus was like, who the fuck are you? You know, we're the Dallas Cowboy cheerleaders.

[B]

I'm so fucking hurt.

[A]

You know, so then. But the. But the command sergeant majors and the people that knew me, and then they were asking, who was I? Because they had double the people. So the people that knew me from Def Comedy Jam and Comic View, they had double the people. So I was doing this big shelvis, a tribute to the King. And I was dressed as Elvis Presley with the mutton chops and the wig and custom made Elvis outfit from BK Enterprise, where Elvis was getting his made. And I was doing this. That was my intro. And people died laughing and everything. And they loved the country singers, and they were waiting for Dallas Cowboy cheerleads. But we went to a fob, a forward operating base in Afghanistan, and you could hear these dudes on their heads, who the fuck is a black girl? I don't know who the fuck she is. And I was telling every day dick joke, every dirty joke I knew. And they were stomping and clapping, and then I could get. I got on the helicopter and they said, whoever she is, protect her. I ain't never laughed that hard. And that's what comedy does, in my opinion.

[B]

Yeah, absolutely. That's amazing.

[A]

It brings us together.

[B]

Same thing with the roast, but so does the military.

[A]

Oh, absolutely.

[B]

I think that's the thing that a lot of people maybe don't understand, like, the camaraderie that exists within the military. It's like when you know that your life is dependent on the person next to you, you don't really care that much that they're Filipino. That's a lot of this shit goes out the window.

[A]

Absolutely.

[B]

So a lot of my buddies that are in the military, they have these, like, incredibly close relationships with guys, like, from all different walks of life. But there's nothing off limits. No, it's not like a regular office job where, like, you would never maybe share your real personality with somebody at the office.

[A]

That's right.

[B]

You're gonna get to know who that person is.

[A]

Absolutely. Cause you're shitting, showering, and shaving with the person. You know, you're eating the same MRE that they're eating. You're telling stories. You're sad that your girl betrayed you, so now you want to shoot somebody. I'm just saying to be facetious, but I think military, it's one of the great law enforcement. Anything that, like, you say, your life's

[B]

on the line, shit gets different.

[A]

But also it's the humor. It's gallows humor. Like people that were so upset about the roast.

[B]

Yeah. What did you. First of all, you had an amazing set. Obviously you've heard this, but, like, you killed it. There was something that I thought you brought to the Rose that was fantastic. Which was one. Genuinely having fun is infectious. Right. Like, whoever has the most fun.

[A]

Yes.

[B]

I want to be around as a person that's consuming yes. Right. The person who's watching the game and they're having the most fun watching the game. That's the part of the bar you want to be around.

[A]

Yes.

[B]

And you were up there. You were having so much fun, and in a way, it broke the fourth wall. There are moments where. And I want to ask you here, it's like, I don't know if you even reading off the prompter, like, are you just making up all this shit? Like, this is a big fucking moment. I did the Brady one. There's a. It's a big moment where you're going, okay, I've been working on this. I want to make sure that everything goes well. But it felt like you were just kind of letting it rip.

[A]

Well, okay.

[B]

So, like, it felt so natural. Yeah.

[A]

So. Okay. Could you. Because a lot of people don't really understand the amount of preparation. It is a production, and they're. And you run in jokes with their writers. Did you guys do that?

[B]

So basically. So I had a few guys that. That were working with me, and they were fantastic.

[A]

Me too.

[B]

Yeah. And, like. And you should have the guys that kind of, like, understand your voice.

[A]

Right.

[B]

And it was not to make this about me, but it was a crazy weekend.

[A]

We're gonna make it about us.

[B]

Okay.

[A]

Yeah. Okay.

[B]

So it was like, I was doing Madison Square Garden Friday, Saturday, and then I had to go do the roast Sunday. So. So basically, I was like, okay, I have two weeks to work on the roast, and then I want to make sure I'm ready for Master Square Garden.

[A]

Yes.

[B]

So it was like this. It was crazy week, but some amazing guys that helped me write. Right. Robbie Slovik, Ryan Nessen, Matt Broussard, Tyler Morrison. I want to make sure I'm getting all the guys anyway, but I had it all kind of mapped out. But there is that part of you when you're up there, you're like, man, I just want to be in this moment. And I felt like the times where I kind of, like, segued away.

[A]

Yes.

[B]

Were, like, the realest Dana White in the audience, and I, like, had a joke on him. Like, there were just these. And I saw you do that. Or at least it felt like you were doing that.

[A]

That's what happened. That's what happened.

[B]

You saw the whole place just get caught up in it. It was, like, the most pure version of what you wanted to say.

[A]

That's right.

[B]

And now, instead of, like, us analyzing the misdirection of your joke, we're caught up on your energy.

[A]

Absolutely. And that's what you want, and that's what American humor is all about. This is an international experience because everybody got Netflix. But I agree with you. For me, I took a meeting with Netflix and I pitched an idea that I wanted to do with them, and they were like, oh, that's interesting. Great idea. Would you do Netflix as a joke? I was like, sure. You want me to do that? So they said, okay, let's start there. So they offered me the Ice House in Pasadena. The hundred plus seat room. Not new. It wasn't. No big room. Right.

[B]

Great room.

[A]

That's right. Very intimate. See, I like the intimacy of the comedy club. Yes.

[B]

There's something beautiful there.

[A]

You can't be.

[B]

The connection is built there.

[A]

That's right. Theaters are great.

[B]

They're amazing.

[A]

But you cannot hold your lemon pepper wings and your drink on your lap at the theater.

[B]

You can literally touch everybody in the club.

[A]

You can slap somebody in the back because you don't know, did you hear what the foxy just said?

[B]

Also, everyone can see everyone else.

[A]

That's right. And it brings people together and you can feel, okay, you don't like this. Okay, let me transition over to that, you know? Cause I'm doing, like, political humor on the road. I'm doing. I'm talking about being a Republican. I'm doing Trump jokes. I'm doing, you know, why the Democrats are gonna continue to lose election jokes. But I'm using every word in the lexicon and telling them why I'm using these words. So in a comedy club, it's more intimate. But I got a couple of calls from my colleagues saying, you too big. You need to be in the Hollywood bowl show. You need to be in the. This, this, this. Why would you do a little bitty room like that? Why not? Why not? If this is where we work? This is where we work.

[B]

I think sometimes people get caught up on, like, the perception of what you instead of, like, what you choose to be doing.

[A]

Yeah, absolutely.

[B]

And I think you've been in the game long enough where, like, maybe you're not as worried about that. I think, like, when people are first getting there, a little bit of momentum.

[A]

Yes.

[B]

And I remember being in that position where it's just like, all right, what should we do? And what is the venue we should be doing?

[A]

Right.

[B]

And then I think after you do those things, you go, well, what do I want to do for where I'm at in my hour?

[A]

There you go. And see, for me, I wanted to do. I asked him, I said, will you allow Me to bring the show that I'm doing. I'm doing the I Need a job tour. Will you allow me to bring that show into the Ice House? They said, sure, whatever you want to do is your night. So it's, I go on first, then it's Kyle Irby goes up. Now Mike Washington usually travels with us, but he. We're all such close family.

[B]

You'll start your own show.

[A]

Oh, absolutely.

[B]

And then you bring up comics.

[A]

Uh huh, uh huh. And that's what I was trying to advance.

[B]

Oh, interesting.

[A]

That's the show that I really want to do because I think that there's a camaraderie of comics. There are a lot of comics out there that think that their career is. They're not gonna have it, but there's some great comics out there that need us to pull em up and go, come on, it's not over for you. You could be Kathy Griffin. Come on, girl. So you had that issue with the head. With the bloody head. Okay, come on back. Tammy Fescatelli, great comic. When you're talking about Melly Camacho, but you're talking about there are a lot of old school comics that need to be put back in the mix. So I asked, could I do that? And then they said, what about BT Kingsley? I was like, cool. So we did the show the way we do it.

[B]

Are you doing time in between? Like if I'm going to see Cheryl.

[A]

Yeah.

[B]

And I want, and I want more than just the opening. Am I going to get Cheryl throughout the whole night?

[A]

You get what I would do as a headliner. You get that up front, you open the whole thing. Yeah, I open the show and you get that up front. And then Kyle comes up and he does the show. But when Mike Weisen is with us, I do what I do. Then Kyle comes up. Then me and Kyle got a banter. Then we bring up Mike Washington and then he does what he does. And then me and Mike got a banter. So it's like being in a comedy team with everybody on the show. And I say it's a house party inside of a comedy club and it's fun. But also we run it. The time is right. Cause it helps me do better on time. Of course, you know, if you want to be in the club all night long. But these people have been here setting up before you were here. Come on, let's get them in, let's entertain and let's feed them them, put drinks and food in them and get them out so they can go Home happy. Right? So. But when doing this for Netflix, this small room, it put my name on the map. So then somebody calls me and says, would you be willing to do the Kevin Hart roast? I said, of course.

[B]

How long before the roast do you agree to it?

[A]

Oh, it had to be maybe a week.

[B]

So you would have to prep.

[A]

No way.

[B]

So everybody else has probably been prepping for at least a month.

[A]

Yeah, I think. I think. I think about. I'm not sure. I don't know. Can somebody ask? Kyle's out there. He'll know the exact time. I know I had enough time to. As soon as they asked and I didn't know if I had it, I started looking for outfits online. Alice and Olivia. Alice plus Olivia is where the outfit came from. And then I went to Amazon. It's this shirt. And I'm thinking, okay, what shoes can I walk in? And I caught my glam guy, Dale McDonald's, and I said, listen, can you come? You coming to town to put my face together for the Ice House show? Can you stay over and do this? And he was like, yeah, I got you. So I pulled my team together. Irna Fouche is my conscious. She runs my foundation. Harry Sutherland runs part of my foundation, and he's the person that hooks me up with corporations because he's an elected county commissioner. So I brought my team in and I said, we're gonna network this, see what we can get out of it. But putting the set together and dealing with their writers because. Did you have to run jokes with their writers, too?

[B]

So what. What. What we basically did was say, hey, does anybody have these jokes?

[A]

Yeah.

[B]

And I knew I was going up at the end.

[A]

Okay.

[B]

So I was basically like, just tell me if anybody has this and I'll just scrap it because I don't want to get to the end of the show. And then a lot of the stuff has been used.

[A]

That's right. That's right. Unless you can make it better.

[B]

If you can make it better, that's fine.

[A]

That's the key. You gotta make it better. Like with the Tony Hinchcliffe, George Floyd joke.

[B]

Yeah, yeah.

[A]

I don't think God sent me a good enough comeback, but because Pete Davidson hit with the Charlie Kirk joke for the Cookout Coalition, I was like, oh, yeah, he got you. Right? He got you. But for me, I wanted to learn to work with other people's writers. And so we could see that they were writing for everybody. And what was working, working. What wasn't working, but what was funny to me, they had the.

[B]

The brunch.

[A]

Oh, the one where.

[B]

Where you're like, yeah, we. Me and Kevin. Yeah, yeah.

[A]

He got. He's making all this noise. He's making all this noise.

[B]

Kevin, shut up before someone thinks I'm

[A]

watching one of your movies. And so I'm taking what they want.

[B]

It looked like you weren't gonna tell it.

[A]

I wasn't. And I was like, move. Go through the teleprompter.

[B]

That was the beautiful moment, like for the. The consumer. Right?

[A]

Yeah.

[B]

It's like, this wasn't supposed to happen. And Kay was like, nah, you gotta tell her.

[A]

But I'm looking at the prompter.

[B]

Yeah.

[A]

And so for me, I like. I like to be prepared so that you know where you can ad lib if you're not. If you're not prepared and you ad lib, you could lose. You don't know what's going on. So in working with them and then Vanessa Gradic and Kyle Irby, Ian Edwards, Chris Spencer, it was a lot of people. I was like, what you got? What you got? But the fact that I could talk to Nikki Glaser at the luncheon. Yeah, okay. So they had the brunch. The community, everybody's there. Get to hug and talk to your colleagues. And I said, nikki, how they coming? They said, they coming for you. I said, what are you coming to me? Fuck's happened? What am I? I'm the bitch that just lost a daytime talk show. I need a job. I need to work. Why they coming at me? And she said, they coming for you hard. And I met Tony at the brunch.

[B]

Yeah, Tony.

[A]

Hans Christ walks up to me. He said, I'm telling you, kids go. I said, I know. And I said, how you coming? He said, I'm coming. Your husband's suicide and you're being raped. No. Jesus Christ. And I said. He said, well, what are you thinking? I said, you better be funny. I said. I said, if it ain't funny. I said, I'm going to get your ass, I swear. I said, I'm going to get. If it ain't funny. I said, it better be funny. He said, well, what about you? I said, my husband been dead, you know. And then that's when I thought, what are you gonna say back to him when he says it? And I'm thinking, what do you say back to him then? And. But he. He's a great villain.

[B]

Yes, he is.

[A]

I think he's the snidely Whiplash of comedy right now.

[B]

He is. If we're looking at comedy as wrestling.

[A]

Yes.

[B]

He is the perfect heel.

[A]

Absolutely.

[B]

Slither it.

[A]

Yeah. But here's the thing about this generation of roasting. It's not like when it was private at the Friar's Club and it was digs against people and we knew each other, we knew it wasn't personal. And then it's not like when Dean Martin and you got Milton Berle, who tells the best. Who has the best dick jokes in the industry. Why? Cause he's got a big ass dick and he was blowing the backs out of starling in the 40s, 50s. Oh, yeah, Milton Burke. Because he's not attractive in the face, but he was throwing that dick on the back. Yeah, he was blowing them bitches out. So for me, it's not the same thing, but they roast at a certain level. Right. But the fact that he came to me with respect.

[B]

Yeah.

[A]

And I said, okay, it better be good. I said, that's all. This better be good. And so Shane Gillis calls me and I said, first people say, well, Shane wants to talk to you. I said, give him my number. Let's talk. And I said, shane, I said, your name. I said, it's great Western. He said, that's what I'm named after. I said, good. I said, if you don't come hard and don't come correct and this shit ain't funny, I said, I'm going to pop you like Doc Holliday in Tombstone. I said, because that's my favorite movie. I love Shane and Tombstone. So we laughed and we joked, but then even running the jokes and having other comics go nah, and then running them through the prompter because I want to get my cadence right. I don't want to be reading something. I want to be feeling and giving life. But I kept asking God on that stage, give me the words. Give me the words that the audience needs me to say.

[B]

What's in the moment.

[A]

Yeah. Because I had a piece of paper. I had a piece of paper. Paper and an ink pen. And me and Tony are sitting next to each other and we're laughing and talking and I'm getting to know him, I'm getting to feel him, that he's not. He's not all the way, this dude, you know, he's the dude that talked about Puerto Rico. But if the Puerto Ricans ain't threw hands on you every time they see you. Yeah, okay. What, what, what is it? Is it.

[B]

People don't want to believe this, but Tony is a very sweet guy.

[A]

He is very much so.

[B]

People will not Want to be as people make up their minds without really understanding who somebody is.

[A]

And that's why I went.

[B]

Austin.

[A]

To do Kill Tony.

[B]

Yeah, I saw.

[A]

I went there to do it because I'm trying. I'm not gonna change you. I don't believe in changing someone.

[B]

Right.

[A]

I believe in influencing them to be their better self and evolution. So you can be that right now because you're making a lot of money. You make a lot of money. That's why I said what I said. And retard. Yeah. Okay. What is the funny word? Little people.

[B]

Yeah.

[A]

Or midget.

[B]

Midget.

[A]

Okay. Disabled, able or retard?

[B]

This is. I mean, retard.

[A]

Okay, There we go.

[B]

Okay.

[A]

But here's the thing. If you push the pendulum too far to politically correctness, then people are gonna fight back with all of what you do. Right. And then.

[B]

Why are you pointing at us?

[A]

That's why I said, I'm glad you white male comics are out there doing what you're doing. Because we were getting cast. You know, GLAAD has me on their website as a homophobe.

[B]

No.

[A]

Yes. For a joke that I told at Comic View. And I thought I was telling a civil rights joke. And they said I was on for. Oh, I would say one day. Because I'm writing a book called I'm Fat because of youf. It's my life story. So I think we're gonna put that story in there. Okay. But the punchline is, Dick is like secret deodorant. Dick is like secret deodorant. It's strong enough for a man, but it's made for a woman. And that's the punchline.

[B]

That's. That's what makes you a homophobe.

[A]

It's all the stuff that I'm comparing it to. To say of our struggle. And you're comparing it to this. And they said I was a homophobe. But I laid it out. I laid it out from the middle passage, the everything.

[B]

All right, guys, listen. You know. You know what a power move is? Yeah. When someone gets fired on a Friday and launches a company by Monday, That's a power move.

[A]

Power move.

[B]

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[A]

being upset about jokes that were told at this roast was racist. Of course it is.

[B]

Yeah.

[A]

It's racial. Of course it is.

[B]

Yeah.

[A]

But when we're looking at you guys say things, then they say, well, it opens the door to this. But Paul Mooney used to walk white people out of Carolina I used to

[B]

watch Paul and Carol. That was one of the most unique comedy experiences because Paul would get these white women. It was also the women. He would get them in their feelings. But Paul. Paul would say wild shit. Don't get me wrong. Yeah, but he was hilarious.

[A]

And it was well written, well constructed. That's right.

[B]

But it was wild.

[A]

Jackie Mac Mason.

[B]

Yeah.

[A]

See, people don't understand. And I'm not giving cover to racism. What I'm saying is, don't get mad. Get motivated. If you are mad about this, then be mad that farmers are now losing their farms in these red states. Be mad that 300,000 women lost a job.

[B]

But they're not gonna do that. Cause there's no clicks or virtue signaling or white knighting based on that. There's no pats on the back based on that.

[A]

Well, here's your problem, though. So you want to talk about a roast that we did with an expectation of us being superheroes, but you go to your job every day and buy from accounting, tells the worst jokes in the world, but you ain't did shit to Bob from accounting. But you want us to stand up. If you and I were on the dais, we were supposed to slap Tony, Right?

[B]

They wanted us to.

[A]

Well, here's the problem. I need you to go to your job and slap the motherfucker that's telling my license. If that's what you want. If we throwing hands. If that's what you're doing.

[B]

We were talking about this on the pod. It was an interesting thing because, like, I think a lot of the outrage maybe came from. This was huge. All over social.

[A]

Yes.

[B]

And when you're looking at, like, your friends, pictures of their kids and vacations, and then all of a sudden, this joke pops up on your screen that you didn't really elect to watch. It's just kind of thrown in your face and you're like, yo, what the fuck is going on?

[A]

Right.

[B]

When you're at home and you choose. Choose to click on the roast of Kevin Hart.

[A]

That's right.

[B]

Knowing it's gonna be wild.

[A]

Right.

[B]

I don't know if people had that much of a reaction. There may be moments where they're like, ooh, that joke was harsh. Or, ooh, do these people really not like each other?

[A]

Yeah. Because I was even like, damn, what? But they didn't want us to know what people were saying, which I think is better. Right? It's a reaction. Yeah, it's a reaction. But then people are, like, criticizing us, saying, well, you sat there and you Laughed. Well, first somebody had to clear that joke. So what I'm thinking is who cleared the joke? So if you cleared the joke, then that's the type of humor we going with, whether it was funny or not funny. But on the same token, it is a roast.

[B]

That's the thing people got. People gotta understand a rose is different than a stand the back.

[A]

That's right.

[B]

And Mark, you had a great way of describing this where you were like, it's like seeing the street fight can be like brutally violent, but then seeing a UFC fight where, you know, this is the point of what these guys are doing and they all signed up for it. It can still be brutally violent, but it's a little bit more digestible.

[A]

Yes, it's digestible.

[B]

It's contextualized. But at the same time, if you're scrolling at 8am and like you're having breakfast with your kid.

[A]

Did you see this?

[B]

And then you see it now I get punched in the face 10 times. You're like, this is so violent. Why does anyone watch this? But it's being pushed on to you.

[A]

It's the algorithm. So if what I said to everybody, I'm not going to get all these interviews, right? And I'm going to come to my thoughts. But here's the thing. Radio stations, everybody that's arguing, DL and Big J going back and forward with each other.

[B]

Yeah. I'm like, what?

[A]

Well, but here's the thing, though. Listen. They giving as good as they got when they put up Big J, the meme of Big J as Roseanne. It was hilarious. It made me laugh. It was hilarious. Right. But then when they pull up up DL's old stuff, I would never do this. That's right. That's right. Okay. That's comics. That's comics.

[B]

We're not perfect. Especially if we're talking on a podcast or like a Talk show for 10 years. We're gonna say some wild shit.

[A]

That's right.

[B]

That is gonna present ourselves as hypocritical if we're white knighting about something, if we're trying to.

[A]

And we are hypocritical.

[B]

Yeah.

[A]

Because we evolve in that state. But you doing radio, time spent listening. So you're arguing about this. You're talking about this. Hey, when we come back, doctor Such and such is gonna talk about his radio reasons why the roast was not applicable. Da da da, da, da, da. Okay. It's time spent listening. It's advertisement now. People that didn't have Netflix now got Netflix.

[B]

Right?

[A]

People that didn't See the roast. Now watch it. So something that had 13.8 now has 15.

[B]

Oh, they told me the roast numbers for Kevin Hart were fantastic.

[A]

Yes, it's big. But you know what I thought the genius was? You put what looked like an attack upon a black female comic up against the manosphere. So if you love Cheryl Underwood and you watching them beat her down right now, you're like, cheryl, do something. Do something. And did something. That's right. If you say anything that sound like you will not make it out of Inglewood. A lie, a rut. This is the forum built by the Showtime. You will respect us in this house. So for me, I. I felt that God sent me, and I was produced to deliver for everybody that thought what was being said was inappropriate.

[B]

So God sent you to call Shane

[A]

a. I believe it. Because, no, I asked him to be able to listen. I'm not talking about you. Kevin has the midget, but I'm talking about you, Shane. That's what. But also that January 6th joke, now, that was written. And I said, that's the one I want. Because I asked Nikki, I said, nikki, give me some pointers. And there's two female comics talking to each other, right? Well, we're supposed to be mortal enemies. White woman, right? Black woman. We're supposed to be mortal enemies, right?

[B]

Are you?

[A]

No, not. Well, society will want us to be mortal enemies.

[B]

Oh, really?

[A]

Chelsea Handler, she comes to me at the brunch and she says, listen, I'm not coming from. I said, listen, I got a couple on you. But they not bad, you know? So we're talking. But that's camaraderie, right? So when Nikki says, tell them to give you the hardest stuff. So some of the stuff they said, I said, that don't even sound like me. No, I said, give me something. We want to make this a great roast. We want to do Kevin proud, right? And for Kevin to say, cheryl, I want you to do what you do. And then for my team to go, here's what you need. Here's where you are at your best. And so. And then I'm feeling the audience. Cause some of the jokes the audience didn't like. Some of the jokes they liked, but they didn't know why they liked it. And then also, Hollywood is jaded. California is jaded. So they not laughing like if we was in Kentucky and they slapping them and we having a good time. But then I thought, nah, you got them moving. Yeah, speak to the room. You got them moving. Speak to the room.

[B]

Oh, you're saying earlier in the roast, maybe they weren't really cooked, because when you were up there, I thought they were standing up.

[A]

They looked crazy. Well, I did not. And, you know, kind of out of body experience because I didn't realize what was happening. What I felt was, okay, Cheryl, there's. Nobody's getting up because I'm listening, and nobody's saying, answer them. Answer them back. Let them know you ain't saying nothing but a motherfucking word. Where the fuck you think you at? You know, this a roast to Kevin Hart. We still black up in this motherfucker. Right. So when you were watching it, what were you thinking?

[B]

I think my biggest takeaway was that it felt like there was some animosity between some of the comics that went up.

[A]

Yes.

[B]

Like, that's why I think it felt a little bit different. Like other roasts. It's like, oh, we all like each other, so there's more love here. But it seemed like there were some people that went up that actually didn't like each other. So that's why some of the jokes is like, ooh.

[A]

But to me, what I felt, and really, I did talk to God. I. I said, listen, I'm up here with my colleagues. These are gentlemen that I'm trying to get to know that I need to understand what is comedy right now. This is what comedy is right now. So, Cheryl, if you're in this game, you better figure out what it is right now. But then I thought, oh, wait a minute. Cause I used to say, ofe cracker peckawood. One of my first jokes that I wrote, what go good with chili crackers. Now that you mentioned white people, let's talk about they motherfucking ass or why do you carry your purse on stage? Cause white folks steal any race of people. Take land from the Indians or shop enough, take two or three dollars out your purse. Those are jokes I'm telling because I'm trying to express the history of this country. Right. But then if you get to do comedy long enough, you evolve into something else. Shane will evolve, Tony will evolve. But if we work together, just think of the type of movies we can make. We could recreate Smokey and a Bandit. I. I said we need to redo smoking the bandit. You be Burt Reynolds, and I'll be Jerry Reid. You know, redo Cannonball Run. Let's get together. All of us as comics should be working on content together so we can keep American humor alive. And we can pay our bills and our mortgages and do things for our foundations, because do you have a foundation.

[B]

I have a foundation I work with. Not my personal. It's not my personal.

[A]

But wouldn't it be great if we all got together and it wasn't just Netflix roasting somebody? How about we roast to benefit something?

[B]

Yes.

[A]

We're good enough that we can roast to benefit something. We can still hit somebody. Not as hardcore, because Netflix, I think that's why I said free speech is alive and well. And I thank you, Netflix. Why? Because I think people push too far into political correctness, the pronouns and stuff. So people got mad because I got to call you a pronoun. You know, like I do transgender. I'm supposed to be transphobic. I'm supposed to be homophobic. And I do all of this in my show where I talk about these things that I'm supposed to be. But you won't get to know me and understand I'm not against you. Just cause I'm pro me don't mean I'm against you.

[B]

Right.

[A]

But some of these things, I just can't. Why are we agreeing with why? Why can't we talk about it? And that's how I looked at me participating in this role. And then I found that I really wanted to get to know everybody. Draymond, scared to death.

[B]

He was scared of you, so.

[A]

No, he was scared to do the roast. So we're in the green room.

[B]

It's terrifying. Imagine someone who's never done comedy before doing on the biggest stage in front of the most people.

[A]

You know what I told him?

[B]

What?

[A]

I said, listen, you play basketball. Yeah. I said, I don't. You coming into what I do, so you don't have to be me. Get through it.

[B]

Yeah. The expectation is definitely lower.

[A]

I said, take a deep breath. I had him call Chris Spring, and I said, you talked to Chris. I said, but even if you get a chuckle, that's your standing off.

[B]

Yeah.

[A]

Even if you get a he, you a trip dreamer.

[B]

Yeah.

[A]

That's a standing oath for you. You're not gonna get what they're gonna get. Cause we've been doing this. We know how to course correct quickly. That joke didn't work. Let's go to something else. We know how to feed off the crowd. This is what we do. If I was playing basketball, that ain't what I do.

[B]

If I hit the rim, I'd be happy.

[A]

Absolutely. If I can just dribble a little bit, you know? But to talk to them, to talk to Lizzo and say, girl, don't worry. Take a deep breath.

[B]

She was another One that did fantastic. Off of energy.

[A]

Yes.

[B]

She seemed like she was enjoying the moment.

[A]

Yes.

[B]

And again, it's a very difficult thing to communicate to somebody who's nervous, to be like, hey, if you just don't be nervous and have fun, it will be great.

[A]

Relax.

[B]

Because it's the hardest thing to do is when you're nervous, just, oh, okay, well, I guess I'll just turn that off and have fun. But the people that can kind of embrace that. I felt bad for Draymond because he kept getting booed by all the Lakers fans. Doing this for the first time, and you're getting booed.

[A]

Yes. But now he. Once you get through it, it's over. I think Naim did a wonderful job, and I really would have wanted Tiffany, while I was getting beat up, to come down and go, hold on, bitch, let me help you with some of this shit. And we show what black female comics can do when we're in it. I thought Regina hall represented a side of the audience that was like, what the fuck is happening?

[B]

She represented the viewer.

[A]

Yeah. And to me, I thought Chelsea Handler had the types of material. The type of material. I was like, God damn, that joke. We talk about them being pussies, and the only reason why they go into Saudi Arabia is to go get the money. I think I thought, hell, yeah.

[B]

Yeah, exactly. Go again this year.

[A]

Yes. But I don't know. You know, my feeling is, I don't know. Like, people say, well, Cheryl, why don't you do international shows? Yeah, I don't know if it translates.

[B]

Yes, it does.

[A]

Really?

[B]

You would translate? Not only would you translate, but, like, you gotta understand. A lot of people learn English through comedy. So the biggest thing that the industry missed is they thought that comedy didn't translate overseas.

[A]

Okay.

[B]

So they wouldn't, like, spend big money on, like, Hollywood comedy movies because they're like, there's no international audience. And when they stopped selling DVDs, the way that they made up for that, you know, money disparity, is international box office.

[A]

Yeah.

[B]

So then they started making all these, like, big action movies because they're like, listen, if they're not really talking, but there's action, they'll watch it overseas. What they didn't realize is that when you go overseas and meet people who speak English, a lot of times they learned English from watching Family Guy. They learned English from watching the Symptoms. They learned English from watching the Wayans brothers.

[A]

Yes.

[B]

Literally, this was a big one. Friends. Or like, Ray. Like the Ray Romano show. What was it? Everybody, it's like, and it's, It's. It's amazing. And Also now with YouTube and so much comedy on YouTube and social media.

[A]

Yeah.

[B]

Since they don't have a comedy channel in their country, they'll watch a lot of their stand up on YouTube.

[A]

Really.

[B]

So I was able to tour internationally for a long time simply just by putting stuff out on YouTube. And now with this success, I mean, I'm sure you'll be able to do it. And they know English. Yeah, that's the other thing. It's like, if you're coming from a small country, you don't have your own, like, film studio that makes all your movies just for you, but you still need to watch tv. So what TV do you watch?

[A]

You watch America? You're right.

[B]

Well, I watch them all the same, dude. When I was in. When I was in the Middle east, because we've done Abu Dhabi, Dubai, we did the Riyadh festival. And like, how was it? It was awesome.

[A]

Really?

[B]

It was awesome. And they did.

[A]

How dirty could you go?

[B]

As dirty as you want.

[A]

Girls can do that.

[B]

Yeah, There was gay girls on it.

[A]

Really?

[B]

Yeah. They killed them. No, no, that's not true. That is not true. They had a falcon just peck at him.

[A]

Get there, get there.

[B]

Attack.

[A]

Well, that's why I'm doing an animated vehicle. And it's for nothing but comedians. And it's how we talk at the roast. How we talk when we're just talking to each other.

[B]

I love it.

[A]

And. And I'm. I'm hoping that Netflix will be interested in that.

[B]

Oh. What I was just. What I was saying about that was that, like, a lot of them are getting a lot. First of all, a lot of them are, like, just getting educated in America, and they're more aware of American isms and culture than Europeans. Really? Yeah. These Europeans, like, a lot of them have, like, built up. They have their own TV shows. They have their own everything. So it's like, yeah, maybe they'll watch a big blockbuster American movie, but not as much.

[A]

Right.

[B]

But if you're from, like, a small country in the Middle east, the only thing you're watching is foreign.

[A]

Really?

[B]

Yeah. They don't have 40 sitcoms that are all made there. There's just not enough people for it. So they're more aware of our, like, slang. They're more aware of our cultural than maybe if you went to France or if you went to Belgium, so you would crush over there.

[A]

Well, I will tell you, it's. I knew something was different in walking through the airport. Yeah, I'm getting stared at. Or. It's not just the flight attendants. It's like really young dudes are gazing at me. I'm like, what's happening? Do you know me or what's happening? And it's all these people that are. I don't know, it's. It's a word for it. What is it? Involuntary celibacy.

[B]

Oh, incels. Yeah, yeah, incels. And voluntary celibates. Yeah, yeah, the incels. Yeah, they're horny.

[A]

Why you laughing?

[B]

Remember when you were in Japan? Remember how horny those guys were?

[A]

Yeah. Oh, my God.

[B]

These guys are hornier.

[A]

Yes. Wait, I wrote to TSA ain't gonna protect you when I wrote. I rode the train in Japan when I was in the military and I was on the train. You know, train. They do some wild shit on the train in Japan. And this dude just walked up and started rubbing my skin. And I was like, what the fuck is. Where's the police? What the fuck is happening? And the translator said, we nuked them.

[B]

And they're different now.

[A]

Never seen it. They've never seen it before. They've never seen anybody alive with this color skin. So they were fascinated by it. But it was stimulating. And I was like, well, get me off the train. Disappear. But to me and a lot of people, that was all. You sold out. They offered you a special and you just took it. Let them crucify the black community like that. That's not what happened.

[B]

What happened was you can't respond to all the. Like, there's always going to be some. There. Someone out there that's going to have negative, critical.

[A]

I felt I need to eat off these jokes. I didn't want. I don't like to record material. I want to be Henny Youngman. Take my wife, please, until I die. I want to. Because I believe you can write jokes every day, but you can only polish them on stage.

[B]

Yes, that's true.

[A]

So do you have jokes in your set that are years old?

[B]

No, not years.

[A]

Yeah. See, I got stuff that's decades old that people. You bring.

[B]

You put out specials already.

[A]

I did Laugh a Palooza with Jamie Foxx and Mark and Jamie Foxx and Marcus came. But I wanted to put the September 11th material on film because I was proud of our country. But I was getting booed when I came out, as I'm a Republican and I'm a. I like a Bush baby. Bush Republican. I was like, get they asses. Get their asses. And the jokes. If you go back and look at the laughter.

[B]

You're saying a woman grew up in a military family that ended up going into the Air Force herself.

[A]

Yeah, but I'm different.

[B]

Crazy idea.

[A]

Well, but, you know, we were Republicans before we were Democrats, you know, and it's. If you. If you. If it wasn't Trump saying things, we would be into a lot of this. Right. But. But Trump and what's happening now. So you voted for this, and now he done shit up. But. But I'm giving both sides.

[B]

Yeah.

[A]

And then you got the Clintons on the other side, which allows you to tell the greatest. That's right. And the greatest dick jokes in the world.

[B]

Yeah.

[A]

Right. So to me, that's the set. But then when Netflix made me an offer I couldn't refuse. Cause I kept saying, no, no, I gotta live off of this. This is how I eat. I don't have a TV show anymore. And I have responsibility, but I also have people who depend on me.

[B]

You can do stuff. We saw you put together stuff on stage. You can't polish it on stage. How'd you do it over all these years?

[A]

But with the roast. See, not the roast.

[B]

I'm saying your act over years. This is decades.

[A]

You can add, too. If something happens on. And I go, oh, what do I want to talk about? But then I lose some things. You know, I got great Oprah Winfrey jokes, but then I lose it. And then do I get to talk about the homosexuality stuff? And then I'm trying to figure out, do I want to bring those jokes back to go. This is how I got canceled. I got canceled from telling this joke. I kind of want to construct a special like that because I want people to get to know me, but I also want people to understand this is what I think is funny. And this is what I want to say. When you were booing me because I said. Said I like President Bush.

[B]

Yeah.

[A]

I want him to get they motherfucking asses right. But you booing me for this. But you. You. You cash the checks that he sent. You hate this, but you cash the checks Now. Trump is a totally different entity. He should have stayed his ass at home. Stop with the Knicks. So we get this over with, we

[B]

be up three zero.

[A]

That's right.

[B]

We have three O's.

[A]

That's right. That's that. You fucking right. But you, you selfish ass motherfucker, you came out here, you fucked up traffic, you did all this bullshit. You should have stayed your ass in the White House.

[B]

Did you go last night?

[A]

No, I was in the vicinity. But the Police told me, stop wandering your little hoish ass around looking for sad Nick's friends to have sex with. There was a lot of them not gonna clean up that night.

[B]

All right, guys, take a break for a second. Talk Space is the number one rated online therapy, bringing you professional support from licensed therapists and psychiatrists that you can access anytime, anywhere. Yes, you're going to be doing this online. Yes. That's how everybody does therapy now. You're no longer going into a little office with, like, shitty artwork on the wall so it doesn't look barren while you bear your soul. You're doing it over the phone. You're doing it over zoom. Talkspace is in network therapy psychiatry. It is covered by most insurers and most insured members pay a copay of $0. Switch providers at no cost. Find the licensed provider that's the right fit for your needs. Talkspace is affordable, even out of pocket. Therapy can be costly. But part of the mission of Talkspace is to provide quality care that is accessible and affordable, whether you or or not you are insured. As a listener of this podcast, you're going to get $80 off of your first month with Talkspace when you go to talkspace.com flagrant and enter the promo code SPACE80. That's S, P, A, C, E. 80. To match with a licensed therapist today, go to talkspace.com flagarant and enter the promo code SPACE80. I've realized something recently. Sleep is everything. I hate to be one of these guys. I genuinely hate it because I like to stay up late and I have to wake up early because I have kids. The reality of the matter is sleep dictates everything. Especially at my age, when you're like 20 years old, I don't even know if sleep is necessary, to be honest with you. And then you hit 40 and it's like, if you don't sleep, there's just no way that you can be a functional human being. I didn't take it seriously until I switched to Brooklyn Bedding. Let me tell you about Brooklyn Bedding. This mattress is different. I'm not just crashing anymore. I'm actually recovering. If you want to wake up feeling aligned, your body actually reset overnight, which is the whole fucking point of going to sleep. I recommend getting yourself a mattress from Brooklyn Bedding. They're not just throwing together some random mattress. They design and build everything themselves in their own factory in Arizona. No middleman, no gimmicks, just quality. And they've got options for everybody. Whatever your sleep style is, they've got something for you. If you like to sleep hot like I do. They actually have mattresses that stay cool all night. Also, this is big, big. They're endorsed by the American Chiropractic Association. So your back isn't going to get cooked while you sleep. And you don't have to stress trying it either. This is the best part. They give you a 120 night trial. If you don't love it, you can swap it out. Simple. So do yourself a Favor, go to BrooklynBetting.com use the promo code FLAGRANT at checkout to get 30% off site wide. That's BrooklynBetting.com promo code FLAGRANT for 30%. Get your sleep right, everything else gets easier.

[A]

Are you a Knicks fan? I'm a sports enthusiast. I'm more football player. I tried basketball players. I'm gonna tell a story in the book. Someone from the 76ers pulled me out of a comedy club and it was the greatest experience. So we're putting it in the book.

[B]

Oh, are you gonna say the name?

[A]

I'm not sure because some of these men, we're gonna change the name to protect the innocent. We don't know if they're married now. You don't know. But it's a great, it's a great story. It's a really great story. It involves the fact that I'm rarely alone anywhere because I just feel like getting gaffled, get fucked up somewhere, you know, looking for Mr. Goodbar. Remember that movie where old girl is out there fucking dudes and the dude stabs her at the end of the movie? Oh, so no spoiler alert. It's a whole movie. But I'm never alone. So the person who knows people have witnessed me be infatuated by somebody.

[B]

I don't want to give the book

[A]

more football players than basketball players.

[B]

But this basketball player, let's just a fake name. Maybe it was his. He was known as Dr. K. No, no.

[A]

If I could have, I would have. If I could. There were a couple of people that I was going to give. Yeah, man, there's a couple of people. I was like, hey, so what are you doing after that? Or they'll say I don't even like no short dark skinned girl. You don't like me now, but you will like me later. I know how to keep a secret. And I got one good skill. One, one good skill that I know. And that's what I talk about in the show. I talk about in the show what I can do and what I can't.

[B]

Do.

[A]

But those jokes, I try not to record them all the time.

[B]

Because you want to hold them for a big moment.

[A]

No, I really like for people to have fun in it because I like sexual material. I like profane material. I like racial material, spiritual material. I talk about abortion. I talk about transgender. Matter of fact, when Shane and I were talking, we almost have the same topic, structure, topic, list. That's right. And so I was like, oh, so I'm going in the right direction. Either you're going to be offended or you're going to laugh real hard. You know, sometimes you people yell out, I came here to hear comedy. Now tell her if there's a white man yelling, hold on, sir, I'm going to get to some material that you're really going to appreciate. Let me get through this.

[B]

10 minutes.

[A]

That's right. Let me get through this political stuff. This political stuff is for them and for us, you know? But that's what I like about comedy. Be able to do topics and.

[B]

Can I ask you a Chicago lore question? Bernie.

[A]

Bernie Mae.

[B]

Bernie is, like, transformative for me in, like, my comedy.

[A]

How so?

[B]

Well, I saw him. I remember watching Kings of Comedy in a movie theater on 11th street and 3rd Avenue with four of my friends, and it was the hardest I've ever, ever laughed. Watching something Eddie was the hardest I ever laughed. Listening. I listened to an audio cassette with my dad.

[A]

Eddie Murphy.

[B]

Eddie. Yeah. Delirious. And I listened to it with my dad. And that big. I think that moment right there made me become a comedian years later.

[A]

Yes.

[B]

But Bernie, it was. I was watching somebody that, like, I just never had seen someone be so naturally funny that I didn't even know if it was jokes. I didn't know if it was a set. I didn't know if somebody that was truly, like, listening to the crowd. Like, the crowd was like an instrument for him. So it was like material. But also, I know how to play

[A]

off of your energy and the words at that time. To talk about the little boy. Yes. And. And hysterical. The F with the 2.

[B]

That's right. That's right. That's right.

[A]

He kind of muffled it when he said him. Downstairs.

[B]

Downstairs to milk and cook.

[A]

Yes, that's right.

[B]

But.

[A]

But most people don't know Chicago. Look, Bernie was a mentor to all of us that were coming up.

[B]

You were watching him when he had his, like. Because he had a room, Right.

[A]

That he would host weekly, that we would go do the room and he would do the cotton, and we would go do the Cotton Club. But we Knew Bernie from the neighborhood.

[B]

He was blue growing up.

[A]

Yeah, he was blue. Cause he was so black. He was blue. That's what we would call it. Hey, what's up, blue. You know? And he would come to my neighborhood because I think he was friends with the Cobb family across the street in my old neighborhood in Chicago. So when we were coming up as comics, matter of fact, it was Bernie that was telling us, dress up. Come on time. You know, he was a mentor to. To us as comics. And when they did the 25th anniversary of DEF Comedy Jam, I ain't afraid of you motherfuckers. And Chris Rock said that one of the people he didn't want to follow was Cheryl Underwood and Bernie Mac. Really, it was Chris Rock said he didn't want to follow either one of us. But Bernie, a big brother to us. And then when they did, when he

[B]

would watch him at that room, what was the name of the room that he would do weekly?

[A]

It was two of them. It was the Roberts, a 600 room, I think. And then he did the Cotton Club. Okay, Cotton Club.

[B]

He's hosting it, right?

[A]

Yes.

[B]

Is he every night just doing different stuff? Is he riffing every night? So it was purely. He was like a magician in a way. Like, he was in his purest form.

[A]

He's a comedian.

[B]

He could just hold attention and, like.

[A]

Absolutely. And for Bernie, if you're talking about the comedians that you look up to and study, because I tell young comedians.

[B]

What can you tell me that I

[A]

need to learn about comedy? I said, find your favorite comic and study mechanics. Yeah, don't take jokes.

[B]

Yeah, yeah. But learn how to tell jokes. Learn how to hold attention.

[A]

That's right, Cadence. That's why the social media comic is good. But if you don't have a point of view and a set structure, what happens when those sketches are not hitting right or your crowd?

[B]

It's different on stage. It's just a different.

[A]

It's a different. You gotta learn it. So Bernie Mac was a. And I would say for me, when I was coming up in comedy, Mitch Hepburn.

[B]

Yeah, Mitch was fantastic.

[A]

So I was in love with Mitch. I was like, if we would just marry each other, we'd be a power couple.

[B]

So you just loved him as a. Did you look, Because Mitch was operating on two frequencies. He was like. You weren't sure if he was playing a character. This was truly him, but you weren't looking at somebody who was being, like, the quintessential straight man. Yes, he was different, and he was on his own. Riff and then he would have these jokes that seem like they could come through a personality like he had, but he's operating on two. Like, you could laugh at him without telling the jokes.

[A]

Absolutely.

[B]

And Bernie had that, too.

[A]

Bernie had it, too. Bill Hicks.

[B]

Hicks. Hicks was like structure, but he was

[A]

intellectually sound, you know, because I'm old school. I'm watching comics. People said, well, did you realize you were a black female comic? No, I really believe that. I'm an old Jewish.

[B]

This is so. Because when I came up, all I was watching was Def Comedy Jam. That was my only real introduction to comedy.

[A]

Really.

[B]

I didn't really know. I never saw Seinfeld do stand up. Like, I knew he had a TV show.

[A]

Yeah.

[B]

So. But that's all that was on TV for me. Yeah.

[A]

See, I'm talking about old school. Lenny Bruce, you know, I'm talking about

[B]

that old school stuff.

[A]

Richard Pryor. I was in a room where Richard Pryor was in the room, and I just felt this energy pulling me. And I felt like, don't do it. Because I'm like, have you ever been in a room with. No, I just stood behind him. I stood behind him and just digested. No. Same thing with Michael Jackson when they were doing those rallies for Michael Jackson to protect him. And I was in one of those events. Right. And sometimes you don't want to walk up to the person. Cause you don't want to break that energy that's pulling you. After the BET Comedy Awards, the first one, Eddie Murphy was in the room. And I ran up to him, but I stopped myself. He's wearing this cold blooded vanilla outfit, vanilla sweater. Had to be cashmere, vanilla slacks. Everything matched. Right. And I almost reached out to touch him, and I pulled back. I said, Mr. Murphy. And he said, I know exactly who you are, Cheryl Underwood. I was like, you know, so when you. For me, I never want to intrude on someone's energy.

[B]

I get it.

[A]

I would rather. Even when I was going to the Republican conventions and going to the dnc, icons in politics, you know, Bill Clinton, very sexual power.

[B]

He felt it.

[A]

Hell, yeah. I used to tell the story about. I put my hand out, drawers just fell down. I was like, what the fuck? I should have wore slacks. Because some people just have this energy and this pull to you, and I think people need to respect, you know, I know people want to run up and take selfies and. And do something sometimes.

[B]

Respect the energy.

[A]

Respect the energy.

[B]

Especially if you really respect the person.

[A]

Absolutely. And it's not like we don't want to. How many people walk up to you and want to take a picture and they don't care what you're doing?

[B]

A bunch.

[A]

I'll be honest.

[B]

Like, as long as in my experience, people have been very respectful. If I'm with my kids or whatever, like, they're almost like embarrassed to ask, I know you're with your family. Would it be possible? And if you approach that energy, I'm

[A]

so that's how I feel.

[B]

Because you're basically going, I know that you're having a moment with your family, but if it's possible. And every single time, if I can, I will.

[A]

When I first did Def Comedy Jam and I said, I told my dad, I said, people were walking up to me, they wanted to talk to me. And he said, well, how many black people do you know will be able to talk to someone they saw on tv, heard on the radio, saw in a movie?

[B]

Great perspective.

[A]

Respect that.

[B]

Yeah.

[A]

But he also said, no matter who the person is, talk to everybody. Like you're talking to Jesus and you can't go wrong.

[B]

Love it.

[A]

Second, your job is no better or no worse, but respect what other people do for a living and respect their time. So for me, and I'm a female comic who's very male directed, I'm very patriarchal. That's why my sets were constructed. When I first started doing comedy, women were popping out of my show like the Great Pumpkin. I'm not sucking no man dick. I'm not doing. And I'm like, but that's why you sitting by yourself? Or that's why you mad that your man is talking to me because I'm not pretty? Like, you know, lies, lies. I'm not the stereotypical aesthetic attractiveness. I'm more intellectual, I'm more energy driven. I'm more like, I can talk sports and politics and current events, but I'm also.

[B]

You're wifey.

[A]

Yeah, but I know, okay, now that's the question then. Let's ask the question then. If I am, then why can't I find him?

[B]

You gotta let them get out their system.

[A]

What do you mean?

[B]

Yeah, like when you're young, when guys are young, they want to wear the cape, you know what I mean? They want to fly around a little bit and have some fun. But like, eventually you don't want like some 23 year old sitting next to you on vacation, just, you know, scrolling her fucking phone the whole time. You're like, I'd rather shoot myself in the head. I want something that I can enjoy and have fun with and love to do that thing you love to do.

[A]

Well, but here's the catch. I think that some men. Absolutely. And I would, like, go. Okay. It depends on how long you want this to be. If you wanted one night, you can have it all. One night. But I'll never talk to you again.

[B]

Ooh.

[A]

What is it? We didn't build nothing. What is this? Do you want to hit it and quit it? I'll show you what hit it and quit it is. And they usually look all pitiful. You know, that's why I sneak out of rooms, because they looking sad. I thought we were gonna.

[B]

No, you say, I see why the guys in Japan was having a hard time. Right.

[A]

But you said you just want. You said. You said you just want this. Okay, I'm gonna give you what you said you wanted.

[B]

But most guys are not used to a woman being as, like, upfront with what she wants as you are.

[A]

Well, it's rarely what I want. I will trade a man.

[B]

Yeah, yeah.

[A]

Intimate. I will trade you for me to get intimacy. In my past, I would trade you an act. Action for intimacy.

[B]

And now you're not going to do that anymore.

[A]

I try not to. Nick's tickets. $150,000 Knick tickets. I gotta do something. Exchange. Ain't no robbery.

[B]

Look for hardwood. That's right.

[A]

And I'm not doing it for the tickets. I'm doing it to show my appreciation that you would consider me worthy of being on the floor where I get to slap Spike Lee and go, man, look at this. But I would like a man to understand, while standup comedy is very strong, it's very sexual thing to do when a woman is doing it. I want to be your companion. I want to be your wife. I want to pick up the dry clean. I want to cook when I come home.

[B]

That's a tricky combo for you, because you need a guy who is not intimidated by your strength and your leadership and your intelligence and, like, the straight talk that you do. Yeah, but at the same time, is. Is. Is confident enough to lead you in certain times, and are you confident enough to let them lead? Is the question.

[A]

Absolutely. If you come to me as a man, yeah, maybe a traditional man, but if you come to me as a man, you're gonna let. Then I'm like, oh, this. This dude. Dude is thorough. He got it. Okay, you ready? It doesn't matter. Race, it doesn't matter. Age doesn't matter. Station in life. However long I got on this earth, I want to find somebody. I Can build with that, understands this is my job. I'm going to do my job. I'm not sleeping with everybody on the road. I'm not doing all this stuff. Matter of fact, I can't wait to come home to you. And most people don't understand when you do stand up comedy, your core quiet. When. Well, you don't want to talk to me.

[B]

I've been talking.

[A]

No, I've been talking. I've been talking. And all this adrenaline is running through my body after the show, so I want to call somebody. How was the show, baby? It was good. Do you miss me? Of course I miss you. When your flight land, I'm looking for that guy that understands you have a job. So do I. Yeah.

[B]

What has been the nature of your relationship history lately? Have you been dating?

[A]

Well, I guess you got to go outside to date. And I'm kind of a homebody, kind of reclusive, but if somebody would ask me out, most, for the past few decades, most men just kind of stare at me or gaze at me, and I think they think I have somebody. So they don't. They don't ask me. They don't, they don't talk. They don't go, sir. So after the show, would you like to go out for coffee?

[B]

They're probably intimidating. You sound like an incel.

[A]

But I, I think, see, I, I've heard that from women. They're just intimidated by your success and your power and your education. I don't know a real man who's intimidated.

[B]

Not a lot of real guys.

[A]

Well, that's right. A real man looks at me as an asset. Yeah, of course, right, if, if you're quiet as a man, but you're still strong, man. What do you mean?

[B]

Assets are expensive. You buy an asset. A home is an asset. Assets are expensive.

[A]

Yeah, but what if we build?

[B]

You ever seen a man buy a home? You know how intimidating that is?

[A]

It's fun.

[B]

It ain't fun when you go and get a loan from the bank and they tell you how, oh, God, gotta pass inspection. That is intimidating. Get in a hotel room for a night, that's, that's easy.

[A]

See, to me, I, I go into it as, okay, what do I need to have this? Would I need to have this? Okay, check it out, check it out. And I sent in my lawyer and I send in my accountant and I go, okay, don't come back without it, and let's go. And I do my job. But see, to me, that's the kind of guy. But then he's more traditional.

[B]

Well, that's what you'll end up with then.

[A]

Yeah, somebody is more traditional. Somebody that understands. I want somebody that I can talk to about things and go, did you hear this? Did you hear that? And then somebody that understands. I don't know everything. Yeah, I may project leadership, but I want you to teach me something. Change, tire. Let's talk about cryptocurrency, which I don't understand.

[B]

Yeah, nobody. Nobody does.

[A]

See, I think it's speculation.

[B]

It is all speculation.

[A]

If you can get your money in there, you know, but see, to me, this is what I wish people would understand about comics. We have to know a lot about everything, and then we have to keep working, and then we have to find other revenue streams making content. So that's why, you know, I'm doing a great American talent search, because I want to bring back the variety show type structure and take it all over America. That's gonna be my next tour.

[B]

Oh, wow.

[A]

After we do this. Because I think there's a way to merge my daytime Persona with the person they saw on the roast. Oh, interesting, right? And do it all over the country and then turn it to maybe a TV show vehicle. But anything is talent. But if you sing or if you are in a singing group, you have to master the past. Classic rock, classic country, classic soul, classic hip hop, classic language. So you have to do some old school stuff that we. Because nostalgia works, of course. But if you're a young person doing it, or if you're the white fire department somewhere doing new addition. Yeah, See, that's gonna bring America together. And they got gospel plays that, you know, we're putting on college campuses, you know, PWIs, HBCUs, community college. Because I think people need to learn both sides of the entertainment business. You think you want to be a performer, but maybe you're not the performer.

[B]

Maybe a director, maybe a writer.

[A]

That's right. Maybe you're audio.

[B]

Yeah.

[A]

Right.

[B]

So.

[A]

And then I want to try to do something that brings jobs back to California because we just want to drive to work and come home and sleep in our own beds.

[B]

There's a lot. There's a lot needs to change for that to happen. You talk about entertainment jobs.

[A]

Yes. How so?

[B]

I think, like, the easiest way of looking at it is to just say, oh, the unions are doing this or the city is making that. I think that probably the more nuanced way to look at it is that for a long time, making a movie in a place like California was not only the easiest, but also the Best. Like you had the most talented crews there. And when I say the crews, I mean like the lighting guys, the audio guys, whatever. And then as equipment got less expensive and as people got trained in other parts of the world, they could start to be competitive. Like you saw what Tyler did in Atlanta.

[A]

Yes, in Atlanta. Right.

[B]

And like that's working within politics, like getting these tax rebates on other things. And like, there are other places in America that did it and there's other places internationally. Like, we just did this movie, Street Fighter, remember the video game? So we shot that in Australia. And I think it's like 60% off to shoot it out there.

[A]

But why can't first the, the right political leadership, the right financial structure.

[B]

So I think what has to happen is like, there's got to be like an incentive, incentive structure. And like, I think the easiest version of it is to just be. Just to like point fingers and blame.

[A]

Yeah.

[B]

But there's another part where you just go, okay, Like, California has been incredibly successful and prolific in making like film and TV for a while now. Other places can make high level film and tv. So maybe California goes okay. In order for us to stay competitive, you have to change something.

[A]

That's right. It's going to have to be a paradigm shift.

[B]

That's the, that's a free market economy like that. If you bring a budget to.

[A]

If you, if I want to make, make a movie and you bring a budget and California says, okay, you do that here and we're gonna help you pay to do that here. I think people have to understand there's so much. The people that I worked with on the Talk, the greatest people in the world. So when I got to the roast and I saw the same people I worked with at the Talk, I felt safe.

[B]

You're like, oh, wow, these people are.

[A]

Yes, that's my cameraman. That's my, that's my teleprompter person.

[B]

That's what you. That's what I mean.

[A]

Trust.

[B]

We're going like, I'm going to film a movie out in California this summer.

[A]

Okay.

[B]

And like, I would imagine it's one of like a handful of bigger budget movies that, that are going to be filmed there. Which is good.

[A]

Yes.

[B]

Because there's nothing about this movie where you need to film it there.

[A]

Yes.

[B]

It was decision made where they're like, we're gonna make this year.

[A]

But did you have to do reasonably price other people places to get to the money, the finance money?

[B]

I, I would imagine there was like good financing behind the Movie. And there was.

[A]

Can I tell you something? Honestly?

[B]

Not.

[A]

Because I apologize for cutting off.

[B]

Oh, please.

[A]

Yeah. But okay, so while I was working at the top and I have people that, like, I'll write the three to five pages and then I'll hand it off to somebody and go, just give me a script. Doesn't have to be perfect. Why? Because the first draft is not the last draft. So I have all the these scripts. You go to the agents, get agency, they tell you why it's not good. Okay. But I just watched some stuff that. This is horrible. So why. How did that get financed?

[B]

Good doesn't always mean it gets made.

[A]

Right.

[B]

So I think what happens without going, like, too inside baseball, like, I think what happens is, like, there are different networks that have objectives. So they go, hey, we're going to make a show for young adult males.

[A]

Yes.

[B]

So you might have the best.

[A]

That's what my animated vehicle is. It's for young adult males.

[B]

So then your agent's got to find the streamer that is looking for something for young adult males. But if you're a streamer that's like, we're looking for 24 to 40 women.

[A]

Yeah.

[B]

You present them that, they might think it's amazing and they might go, it's just not what we're looking for. They might choose a shittier project.

[A]

Yes. That actually fits their Right. Was for. For me. Now, for people that say you sold out by agreeing to do a Netflix

[B]

special, why is that selling? What's the argument for that?

[A]

Because there are people who believe that we just sat there and took the beatdown of our culture for money from Netflix. But what I want people to understand is this is the business we're in. I was called to do a job. I believe I did the job. While I also defended the culture and did. Defended American humor, couldn't you also say,

[B]

like, just being up there is representative of the cult? Like, the culture isn't one thing I would imagine it's just like saying, like, Latinos, their culture is just salsa. It's like it's not just that.

[A]

Right.

[B]

And like you being on that stage and having that prolific set and being the talk of the industry.

[A]

Yes.

[B]

You could make an argument that that's a huge contribution from the culture.

[A]

That's what I would want people to see and to see.

[B]

Well, that's what we'll see stick. Like, the controversy lasts for a few weeks and then goes away. So it's like your longevity after this moment is the culture's longevity.

[A]

That's Opportunities. Opportunities. I wouldn't have these opportunities.

[B]

Now, you don't think these other. You don't think these other streamers are seeing what you do, what you did right there, and they see that you get a deal and then let's say your Netflix special goes crazy. This is a, like, the industry is a game to be second, not first. So you don't think that they're having their board meetings going like, who's the next Cheryl?

[A]

What if we could get another Cheryl?

[B]

That's how it works. That's the game.

[A]

It's like, it's like. It's like, do you want Cheryl? I can't get her.

[B]

We can't afford Cheryl. Who is. Who is next?

[A]

Or they'll say, get me. And then they'll. Then you.

[B]

You could create a lean. So that's.

[A]

And that is the goal. And the goal is for me.

[B]

And that's what I think sometimes maybe is lost with, like, what Kevin's contribution has been.

[A]

That's right.

[B]

Like Kevin's contribution to entertainment. And I think a lot of times maybe we're used to it because a lot of us grow up seeing black people in, like, these amazingly high positions in entertainment in terms of, like, the comedians that we look up to or the actors, et cetera. But, like, that also needs to be maintained.

[A]

Yes.

[B]

So, like, Kevin being acting and doing stand up, but also, like doing all these advertisements. Like, think about what that. Like, this is. Again, we kind of get used to

[A]

shit showing that we can do that.

[B]

Being an investor. A business owner.

[A]

A business owner.

[B]

But also, like T mobile being like, I want the face of my company to be that black guy. Do you think 40 years ago.

[A]

No, you know what I mean?

[B]

Like, do you think these. These companies 40 years ago where a black. They're having a board meeting, they were like, can we make a black person a face apartment?

[A]

Even now. Yeah, even now. But. Even now.

[B]

But that's the shit that kind of gets lost a little. Not saying that we can't make things better. We should always try to make things better. But maybe there's a little focus where we look at, like, the success. And I would hope that would also be celebrated in this moment.

[A]

That's why I said, you're not just a great comedy. You're a hell of a businessman, because that's what they did. Something that makes something and continues to grow. When we had a black comedy explosion happened, did people think that one day there was not going to be a WB where there was not going to be a upn this is downstream from it.

[B]

And I don't know that maybe that's why I get caught up. And I'm like. I understand that, like, the reflexive nature, like, you just react in a minute, in the moment to something. But, like, when things explode, so many other people are given opportunities to make so much, and it's. It's. You know, to me, like, I'm so grateful for, like, the people that, you know, really kind of put me on. So Charlemagne, the God.

[A]

Yes, Rogue.

[B]

And it's like they both.

[A]

Charlemagne is where my book is being done, of course. Yeah. Yeah. And so for me. But here's the catch, though. What? Trying to get somewhere. And then it's Cheryl before the roast and then Cheryl after the roast, where now people are taking my call, or now the agents want to, okay, go out this. This, this.

[B]

Look at all those opportunities. So it's like, now that's. That's what these things can create. So.

[A]

And prepared content. But now what. And I wish this for. I'm gonna say specifically female comics. It's not just you getting on, or it's not just you doing a movie. Okay. Now we're gonna produce. Now we're gonna make content. We're gonna make animated stuff. Not just for us. We're gonna make it for the marketplace. Right? So we should be making sitcoms and movies. And then we should say, okay, you only gonna give me 250,000. I'm gonna make the movie for 250. 50,000.

[B]

It's a show. She has, like, a micro drama, I think, or something like that. Have you heard about sra?

[A]

Yeah.

[B]

And it's getting, like, hundreds of millions of it, like. And again, it's a different metric that they're trying to understand because it's like short form on your phone, whatever. But I'm saying, like, these.

[A]

It's the thing. Have you seen it? It's on your phone. And it's always abroad that she meets up with the millionaire that wants to hide his identity. And then somebody slaps her, and he's on the phone going by stock and put that out of that. Slap my girl. But I thought you were the chauffeur. And then it's. It goes for a minute or two, and then you buy the other minute or two. And I'm addicted to this stuff.

[B]

That's. And again, this is like big explosions create tons of opportunity for other people. And I get the reaction I get, and people have to feel whatever they want to feel. It's America. You were here in this country you could feel whoever the fuck you want to feel and say however you want to say about it. That's the beautiful thing about it. But there is also. On top of that, there's also potentially, when these moments are really successful, so many opportunities for other people that are aligned with these moments without even realizing it. And that is the cool payoff that I think happens over the next few years. And then we forget about the controversy, and then we just end up seeing. When we were growing up, it was like you're watching the Wayans brothers and you don't even realize how that might be downstream.

[A]

That's right.

[B]

Happened 10 years before.

[A]

That's right. And how can we help each other? Well, that's galvanized.

[B]

You know, this is the moment.

[A]

This is the moment. That's why I'm coming around to talk to people that I would never have been able to talk to and say, oh, let's make this type of thing, or. Or how do I structure this? Or who would I come to finance it? That. That's my biggest problem with people that want to live in their own little silo. So if you don't step out of that silo, you will never understand why Netflix is now interested in Sherlonden Wood.

[B]

You could have fought the other comedians at the roast. Or you can go on their shows, go on their podcasts, collaborate with them on projects, and to get to know

[A]

them better, because these are my colleagues.

[B]

More opportunities for people that you really love that might not be afforded those opportunities now that you're in a position to shine some light on people, that's

[A]

my job, to open the door. That's why it's leadership. Am I right? That's what I'm talking about. Cheryl Underwood, ladies and gentlemen. Thank you so much for being here. You're awesome. This was fun. So let's figure out how we going to make some money.